Fluorinated carbohydrates as potential plasma membrane modifiers and inhibitors. Synthesis of 2-acetamido-2,6-dideoxy-6-fluoro-D-galactose |
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| Authors: | M Sharma G G Potti O D Simmons W Korytnyk |
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| Affiliation: | 1. H.E.J. Research Institute of Chemistry, International Centre for Chemical and Biological Sciences, Karachi, Pakistan;2. Department of Chemistry, N.E.D. University of Engineering & Technology, Karachi 75270, Pakistan;3. National Centre of Excellence in Physical Chemistry, University of Peshawar, Peshawar-25120, Pakistan;4. Department of Physics, University of Peshawar, Peshawar-25120, Pakistan;5. Department of Chemistry, Faculty of Applied Science, Umm Al-qura University, Makkah Almukkaramah, Saudi Arabia;6. Department of Chemistry, Abdul Wali Khan University, Mardan-23200, Pakistan;1. Space Science Institute, Boulder, CO 80301, USA;2. Jet Propulsion Laboratory, California Institute of Technology, Pasadena, CA 91109, USA |
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| Abstract: | Reaction of benzyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-mesyl-alpha-D-galactopyran oside with cesium floride gave benzyl 2-acetamido-3,6-anhydro-4-O-benzyl-2-deoxy-alpha-D-galactopyranoside instead of the desired 6-fluoro derivative. Acetonation of benzyl 2-acetamido-2-deoxy-6-O-mesyl-alpha-D-galactopyranoside gave the corresponding 3,4-O-isopropylidene derivative. The 6-O-mesyl group was displaced by fluorine with cesium fluoride in boiling 1,2-ethanediol, and hydrolysis and subsequent N-acetylation gave the target compound. In another procedure, treatment of 2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-alpha-D-galactose with N-(diethylamino)sulfur trifluoride gave 2-acetamido-1,3,4-tri-O-acetyl-2,6-dideoxy-6-fluoro-D-galactose which, on acid hydrolysis followed by N-acetylation, gave 2-acetamido-2,6-dideoxy-6-fluoro-D-galactose. |
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